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Summer, 1989- (before technology took over, thank God!).
I love how I lost my virginity even though most people say it was r***. I was 11 years old and I had a crush on a guy who would do odd jobs for my mom. He was about 20-22. One day, he asked my mom to go get some tools at a store, I begged to stay behind to play on my swing. My mom relented.
As soon as she was gone, I ran into the house. I had wanted to have s** with this guy, the first time I wanted it. I asked him just to see his p****. He led me to my parents bedroom, laid down a towel, then picked me up and laid me on the bed. He first took my shirt off and sucked my little knobs. Then he kissed my belly all the way down to my elastic shorts. Very slowly, he removed them and then removed my lacy, flowery underwear. I was so excited! My little hairless p**** was fully exposed.
I looked over and he was down to his boxers. He had me remove them. My first sight of an erect p**** was wonderful. I wanted it in me! He clmibed on top of me, put some of my mom’s KY all over my p****. And he then rubbed his c*** all around my lips. Then with one thrust, he was in me. I scream out, and he puts his hand over my mouth. Then he slowly begins ti thrust, he takes his hand off as the pain subsides and I enjoy doing it. He kisses me and he cums inside me, I feel it gush out so quickly and alk this white hot mess comes out of my v***** with blood stains and bits of torn skin (hymen). Afterwards, he cleans my v***** out with his tongue. I see his p**** covered it blood and bits of skin. He leaves and brings back a basin of cool water and soap and he washes my p**** and thighs off. And his own p**** as well. After he cleans up, he lays next to me and wraps me in his arms and cuddles me for ten minutes.
By the time my mom got back, I was in my treehouse and he was fixing the back porch light. God, thst was an amazing day. He worked for us the rest of summer. 

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.